Trimethylsulfoxonium iodide

Base Information

• Chemical Name: Trimethylsulfoxonium iodide
• CAS No.: 1774-47-6
• Deprecated CAS: 76570-08-6,305859-81-8,1646683-13-7
• Molecular Formula: C3H9IOS
• Molecular Weight: 220.074
• Hs Code.: 29309070
• European Community (EC) Number: 217-204-2
• NSC Number: 71213
• DSSTox Substance ID: DTXSID001014581
• Wikipedia: Trimethylsulfoxonium_iodide
• Wikidata: Q15427957
• ChEMBL ID: CHEMBL283149
• Mol file: 1774-47-6.mol

Synonyms:Trimethylsulfoxonium iodide;1774-47-6;Trimethylsulphoxonium iodide;Trimethyloxosulfonium iodide;Sulfoxonium, trimethyl-, iodide;Trimethyloxosulphonium iodide;Trimethyl sulphoxonium ioidie;MFCD00011899;Sulfoxonium, trimethyl-, iodide (1:1);S,S,S-Trimethylsulfoxonium iodide;Trimethylsulfoxoniumiodide;EINECS 217-204-2;NSC 71213;Sulfonium, trimethyl-, iodide, oxide;EC 217-204-2;C3H9IOS;Sulfoxonium, iodide;trimethysulfoxonium iodide;Sulfonium, iodide, oxide;trimehylsulphoxonium iodide;tri-methylsulfoxonium iodide;trimethyl sulfoxonium iodide;trimethyl-sulfoxonium iodide;C3H9OS.I;SCHEMBL2584;SCHEMBL2586;trimethyl sulphoxonium iodide;trimethyl-oxosulfonium iodide;trimethyloxo sulfonium iodide;Trimethyl-sulphoxonium iodide;trimethyl oxosulphonium iodide;tri-methyl-oxosulphonium iodide;Trimethyl-sulfoniumoxide iodide;S,S-Trimethylsulfoxonium iodide;C3-H9-O-S.I;Trimethyl(oxo)-sulfanylium iodide;DTXSID001014581;AMY24038;BCP13230;NSC71213;TriMethyl?sulfoxoniuM?iodide(TMSOI);AC7850;NSC-71213;trimethyl(oxo)-??-sulfanylium iodide;WLN: OS1&1&1 &Q &I;AKOS015833276;CS-W018549;Trimethyl(oxo)-gamma-sulfanylium iodide;AS-12135;SY002188;LS-148154;FT-0633832;T1065;J-200120;J-650228;Q15427957;F0001-0645

Chemical Property of Trimethylsulfoxonium iodide

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Melting Point: 208-212 °C (dec.)(lit.)
• PSA: 36.28000
• Density: 1.7074 (estimate)
• LogP: -2.62070
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: H2O: 50 mg/mL, clear
• Water Solubility.: 15 g/L (20 ºC)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 219.94188
• Heavy Atom Count: 6
• Complexity: 53

Purity/Quality:

99%+ ^*data from raw suppliers

Trimethylsulfoxonium iodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C[S+](=O)(C)C.[I-]
• Uses: Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5 Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides. Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

Technology Process of Trimethylsulfoxonium iodide

There total 6 articles about Trimethylsulfoxonium iodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + methyl iodide (74-88-4) → trimethylsulfoxonium iodide (1774-47-6)

Guidance literature:

at 70 ℃; for 48h;

DOI:10.1055/s-0036-1588971

Reference yield: 28.0%

dimethyl sulfoxide (67-68-5,8070-53-9) → Na4(triiodide)3I(dimethylsulfoxide)15 + trimethylsulfoxonium iodide (1774-47-6)

Guidance literature:

dimethyl sulfoxide; With water; sodium hydroxide; at 20 ℃; for 0.5h; Ultrasonication;

With methyl iodide; at 20 ℃; for 144h; Ultrasonication;

DOI:10.1039/c1cc11898f

Reference yield:

acetic anhydride (108-24-7) + 3-O-(β-D-galactopyranosyl)-D-arabinose (61272-23-9,130767-77-0,130767-78-1) + methyl iodide (74-88-4) → Ethyl methyl sulfoxide (1669-98-3) + 1,3,4-tri-O-acetyl-2,5-di-O-methyl-D-arabinitol (100758-68-7) + 1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl-D-galactitol (19285-93-9,19318-49-1,20316-14-7,25665-99-0,53403-07-9,81600-01-3,83290-15-7,103729-41-5,114183-58-3,25521-30-6) + 1,3,5-tri-O-acetyl-2,4-di-O-methyl-D-arabinitol (19318-22-0,19318-27-5,84885-38-1,84925-47-3,100758-67-6) + trimethylsulfoxonium iodide (1774-47-6)

Guidance literature:

With sodium tetrahydroborate; perchloric acid; trimethylsulfoxonium iodide; trifluoroacetic acid; In dimethyl sulfoxide; Product distribution; Improved methylation analysis; other saccharides;

DOI:10.1016/0008-6215(84)85106-X

upstream raw materials:

dimethyl sulfoxide

methyl iodide

acetic anhydride

3-O-(β-D-galactopyranosyl)-D-arabinose

Downstream raw materials:

2-(4-methoxyphenyl)-but-1-en-3-one oxime

O-<1-(p-Methoxy-phenyl)-2-hydroxy-imino-propyl>-2--buten-(1)-on-(3)-oxim

3-(4-Methoxy-phenyl)-but-3-en-2-one O-methyl-oxime

Dimethyl-oxo-sulfonium-

Refernces

• 1、 Noeske, Tobias,Trifanova, Dina,Kauss, Valerjans,Renner, Steffen,Parsons, Christopher G.,Schneider, Gisbert,Weil, Tanja. "Synergism of virtual screening and medicinal chemistry: Identification and optimization of allosteric antagonists of metabotropic glutamate receptor 1". . p. 5708 - 5715. Retrieved 2009.
• 2、 Duarte-Ruiz, Alvaro,Nunez-Dallos, Nelson,Garzon-Tovar, Luis,Wurst, Klaus,Avella-Moreno, Eliseo,Gomez-Baquero, Fernando. "Synthesis and structure of [Na4(DMSO)15][(I 3)3(I)]. Self-assembly of hexacoordinated sodium". . p. 7110 - 7112. Retrieved 2011.
• 3、 -. "Deuterated antidepressant medicine". Paragraph 0009-0010; 0013-014. . Retrieved 2019/01/23.
• 4、 -. "1-[(4-HYDROXYPRIDIN-4-YL) METHYL]PYRIDINE-2(1H)-ONE DERIVATIVES, PREPARATION METHODS AND USES THEREOF". Paragraph 0064. . Retrieved 2013/03/28.